Asking teams of drinkers complex questions inside crowded New York City bars is hardly a trivial pursuit for Adam Kesner. In fact, the popular quiz-night host wants to make it his livelihood.

"I didn't realize this was a career," said Mr. Kesner, 32 years old, host and co-founder of "Trival Dispute." "I don't think it was a career five years ago."

Mr. Kesner and a friend launched their series of pub quizzes in 2007 after, in true entrepreneurial form, they attended several and thought they could do a better job. A little more than five years later, Mr. Kesner hosts four trivia nights a week at bars in Manhattan and Brooklyn, where teams of regulars compete for shots of alcohol, bags of dollar-store prizes and small bar tabs.

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Adam Kesner, the host and co-founder of 'Trivial Dispute,' during an event at Alligator Lounge in Williamsburg
Jennifer Weiss for The Wall Street Journal

Quiz

Across the country, trivia nights have transformed from low-key events to franchised, money-making ventures.

The Denver-based company Geeks Who Drink employs fact checkers, graphic designers and question writers to compose multimedia quizzes run by their "quizmasters" at bars in 27 states, according to the company.

Stump! Trivia, started in Massachusetts in 1999 and purchased by a California-based company in 2011, has about 230 part-time "trivia jockeys" who run 250 trivia competitions a week across the country, according to founder Bob Carney.

On Yelp, a search for trivia nights in New York City brings up more than 300 results, and at least two companies have sprung onto the scene. The Big Quiz Thing started in 2002 and runs monthly bar trivia shows in four cities, in addition to private events and "trivia writing consulting." TrivWorks customizes trivia events for corporate team-building, some featuring NY1's Pat Kiernan, a former game show host and trivia fan.

Noah Tarnow, founder of the Big Quiz Thing, said when he started the company in 2002, there were only a handful of trivia nights in the city, and he frequently had to explain the concept to people. Now, the market is flooded. "There's a lot of competition," he said.

The twice-yearly "Trivial Dispute" Tournament of Champions drew about 75 people to the Alligator Lounge in Williamsburg on a recent Saturday afternoon. One team, Stinkeye of the Tiger, attends Mr. Kesner's trivia nights on a weekly basis, with team members including a film producer, a lawyer, a doctoral student in psychology and a screenwriter.

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The Stinkeye of the Tiger trivia team at Alligator Lounge in Brooklyn.
Jennifer Weiss for The Wall Street Journal

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"We like knowing things that other people don't know—that seems to be a point of pride," said Jiun Kwon, a video editor on the team. "And we are very competitive."

"Competitive dorks," added her teammate Ian Springer, a screenwriter.

The tournament saw Mr. Kesner and his "Trivial Dispute" co-founder, Gavin Shulman, run through themed rounds on topics such as goats and blue moons, the latter a nod to tournament sponsor Blue Moon Brewing Co., which gave away six tickets to a Brooklyn Nets game to the winning team.

They may be drinking and socializing between rounds, but participants at Mr. Kesner's events take the game seriously, and he rarely has to reprimand people for shouting out answers or checking their phones. During the tournament, Greg Chin, an adult-education teacher, lighted up when Mr. Kesner asked contestants to name the only person to have come in second in three presidential elections.

"This is my question!" he said, before writing the answer (William Jennings Bryan).

"I'm a history buff," explained Mr. Chin, 27, before lamenting that the questions weren't more difficult.

Over the course of four hours, Messrs. Shulman and Kesner entertained the crowd with banter that riffed on cultural references and was heavy on sarcasm. The tournament included two audio rounds, as well as several flash rounds of movie-title mashups, during which Mr. Kesner offered descriptions of two movies whose titles combine. For example, " Jack Ryan struggles to connect with inner-city students." (Answer: "Clear and Present Dangerous Minds.")

While the evening may be competitive, contestant Price Manford said some of the fun was in spending time with fellow trivia fans who appreciate the amount of effort Mr. Kesner puts into his questions.

"The questions are so long, they're so involved," he says. "There's some camaraderie with other kids…because everyone knows weird, weird stuff."

The "Trivial Dispute" rounds are composed of questions of increasing difficulty. "It would be very easy to write six stumpers for every round, but I try and order them," Mr. Kesner says. "Everyone should get question No. 1; one team should get question No. 6."

The night is about showmanship as well as brains. "There's some flair involved in hosting the event," says Mr. Kiernan, whose public trivia nights with TrivWorks have drawn between 200 and 300 attendees. "But what ultimately makes it fun and exhilarating and makes you want to come back is the material hitting that sweet spot between challenging and not too challenging."

Mr. Kesner hosts private parties and corporate events and plans to franchise "Trivial Dispute" along the East Coast, hiring hosts to belt out his questions at bars for a fee. This summer, he hopes to launch a trivia tour bus, with questions geared at New York City neighborhoods. The tentative title? "Trivial Commute."

For now, he'll continue searching for questions that will keep his trivia night a hit among hundreds in the city. It isn't an easy task: "If you make it too hard, nobody is going to show up," he said. "It doesn't become fun anymore. More than anything, this is entertainment."

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